Bucktown has a way of making life feel effortless—brick-lined streets, side blocks covered in greenery, and that perfect “city, but cozy” energy. For their engagement session, Maddie & Shane leaned fully into what felt most them: a relaxed afternoon in their apartment with their dog, Ozzy, followed by a celebratory round of drinks at a neighborhood cocktail spot, Truce for iconic The result? A playful, low-pressure, intimate story captured on film.
If you’ve ever wondered, should we do engagement photos at home, or felt unsure about a photos at your neighborhood watering hole, this is your sign that the best sessions are the ones that match your real life.
Part 1: Cozy at home
We started at Maddie and Shane’s apartment in Bucktown with their pup, Ozzy. It wasn’t part of the plan but after seeing how cozy their apartment was, and how the afternoon light was pouring in, we decided to linger. Things felt easy and natural and Ozzy was able to relax, curled up on his favorite chair.
Taking engagement photos in your home adds a unique element and layer of comfort to your session. How special to have photos in a space that respresents you?
A couple of tips for at-home engagement sessions:
- Choose a time of day when you notice the light is particularly wonderful
- Don’t worry about cleaning up every corner of your space – it doesn’t have to be perfect. We’ll focus on certain areas that are well lit, framed nicely, or are particularly interesting / special to you. If we need to move anything around, we can do that as we go 🙂
Why we shot it on film (and why it fit the vibe)
This session was captured on 35mm and 120 film, and it matched the mood perfectly: timeless, a little grainy, and very “you are here.” Not to mention beautifully rendered rich colors. Film engagement photos have a way of making even the simplest moments feel cinematic
If you’re considering film engagement photos, plan for:
- Slightly slower pacing (which sometimes actually helps you relax)
- Trusting your photographer’s light choices
- Fewer “spray and pray” frames, more intentional storytelling
Part 2: Cocktails
From their apartment, we walked a few blocks down the street to their favorite cocktail bar Truce. The sun was pouring in and the temperature was so nice they had the front windows open. For couples searching cocktail bar for engagement photos the best choice is usually the one that:
- Has a bar top with space to lean in and interact naturally
- Has warm, directional lighting (lamps > overhead fluorescents)
- Offers an earlier, quieter window (right when they open is gold)
I always recommend calling the bar ahead to get permission to photograph there. Some places are very accommodating and some may even offer to let us come in a bit before they open to the public so we can have the place to ourselves
Part 3: Lakefront
After cocktails, we visited the spot where Maddie & Shane had their first date. With views of the Chicago skyline, boats in the harbor, and blue hour lighting, we ended the day on a quieter note. Spending this time with Maddie & Shane really helped me get to know them better and get a glimpse into what makes their story unique.
Takeaway: Make it personal, make it fun
Maddie & Shane’s engagement session proves you don’t need a big production for images that feel special. Start where you’re most yourselves, end with a celebratory drink, and let the day unfold with a relaxed rhythm. The best sessions aren’t about “perfect posing”—they’re about connection and personality!
